WO2022193351A1 - 用树莓苷提高卷烟产品香气的方法 - Google Patents

用树莓苷提高卷烟产品香气的方法 Download PDF

Info

Publication number
WO2022193351A1
WO2022193351A1 PCT/CN2021/083058 CN2021083058W WO2022193351A1 WO 2022193351 A1 WO2022193351 A1 WO 2022193351A1 CN 2021083058 W CN2021083058 W CN 2021083058W WO 2022193351 A1 WO2022193351 A1 WO 2022193351A1
Authority
WO
WIPO (PCT)
Prior art keywords
raspberry
fragrance
cigarette
aroma
cigarette paper
Prior art date
Application number
PCT/CN2021/083058
Other languages
English (en)
French (fr)
Inventor
雷声
王凯
付磊
何靓
曲荣芬
张健
刘娟
冒德寿
李智宇
Original Assignee
云南中烟工业有限责任公司
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 云南中烟工业有限责任公司 filed Critical 云南中烟工业有限责任公司
Priority to EP21878763.8A priority Critical patent/EP4085769B1/en
Publication of WO2022193351A1 publication Critical patent/WO2022193351A1/zh

Links

Images

Classifications

    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B3/00—Preparing tobacco in the factory
    • A24B3/12—Steaming, curing, or flavouring tobacco
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/281—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed
    • A24B15/282—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed by indirect addition of the chemical substances, e.g. in the wrapper, in the case
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/302—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by natural substances obtained from animals or plants
    • A24B15/303—Plant extracts other than tobacco

Definitions

  • the invention belongs to the technical field of tobacco, and in particular relates to a method for improving the smoking quality of mainstream smoke of cigarette products and the characteristic smoke aroma of side-flow smoke by using raspberry glycosides.
  • the tobacco flavoring technology in the prior art mainly focuses on adjusting or improving the smoking sensory effect of mainstream smoke, and does not pay attention to the sensory effect of sidestream smoke aroma; and sidestream smoke aroma can bring pleasure odor, and create a better odor environment for the surrounding non-smokers.
  • the flavors and fragrances in the prior art are insoluble in water, such as the flavor raspberry ketone, which can only be dissolved in ether or volatile oil, which brings security risks to the flavoring of tobacco.
  • raspberry is a functional ingredient in raspberries
  • the chemical name of raspberry is 4-butanonylphenyl- ⁇ -D-glucopyranoside or raspberry ketone- ⁇ -D-glucopyranoside
  • the molecular formula is C 16 H 22 O 7
  • the CAS number is 38963-94-9.
  • the structural formula of raspberry is shown in Figures 1 and 2.
  • the state of raspberry is a white or off-white crystalline powder, easily soluble in polar solvents such as water and ethanol, and has no odor at room temperature.
  • Raspberry glucoside has special physiological functions and biological activities, which can effectively hinder the formation of tyrosinase and inhibit melanin.
  • the use of raspberry glucoside reported in the prior art is mainly used for advanced whitening, freckle removal, anti-aging and conditioning. in cosmetics.
  • the invention aims to use flavors including raspberry glycosides to be dispersed or dissolved in a solvent to form a flavor dispersion, and then added to cigarettes, so as to improve the identification of cigarette products, improve the characteristic sense of the measured cigarette aroma, and improve mainstream smoke It improves the smoking quality, broadens the richness of product styles, and solves the problem that flavors and fragrances in the prior art are not stable enough to affect the quality stability of cigarettes.
  • the invention discloses a method for improving the aroma of cigarette products by using raspberry.
  • the aroma including raspberry is dispersed or dissolved in a solvent to form a aroma dispersion, and then added to the cigarette.
  • the flavor dispersion is added to cigarette paper, cut tobacco or reconstituted tobacco leaf to enhance sidestream smoke characteristics and/or improve mainstream smoke draw quality.
  • the solvent is water, ethanol or a mixture of both.
  • the fragrance dispersion also includes other fragrance ingredients.
  • the other flavor components include one or more of mogroside, maple extract, dihydrokiwifruit lactone, and strawberry aldehyde.
  • the fragrance in the fragrance dispersion comprises: 1 raspberry side and mogroside, the mass ratio of the two is (2-8): (1-3); or 2 raspberry side, mogroside, Maple maple extract and dihydrokiwifruit lactone, the mass ratio of the four is (2-8):(1-3):(0.5-1):(0.05-0.1); or 3 raspberry glycosides, Luo Han Guo sweet and glucoside strawberry aldehyde, the mass ratio of the three is (2-5):(2-5):(0.1-0.3); or 4 raspberry glycoside, mogroside, maple maple extract and strawberry aldehyde, the quality of the four The ratio is (2-5):(2-5):(0.5-1):(0.1-0.3).
  • the fragrance dispersion also includes fillers and combustion accelerants.
  • the filler is light calcium carbonate.
  • the combustion-enhancing agent is an organic acid metal salt
  • the organic acid metal salt is one or a combination of two or more of potassium citrate, potassium malate, potassium lactate, and potassium acetate.
  • the fragrance dispersion is coated on the cigarette paper, and the coating rate of the fragrance is 0.1wt% to 1wt% (that is, the percentage by weight of the fragrance in the dry weight of the cigarette paper), and the obtained cigarette paper has a quantitative weight of 28-38g /cm 2 , the air permeability is 30-100 Coresta.
  • the present invention uses raspberry as a latent flavor for the first time in cigarettes.
  • the invention adds flavor dispersion including raspberry into the cigarette, and solves the problems that the flavor in the cigarette is not stable enough and the style characteristics are not prominent.
  • the raspberry glycosides of the present invention are heat-stable latent fragrances, which are very stable during storage and transportation of reconstituted tobacco leaves, cigarette papers or cigarette products, with no smell. When heated or ignited for smoking, the characteristic components of raspberry ketone can be released to produce the characteristic aroma of raspberry and blueberry. suction quality.
  • auxiliary spice ingredients selected by the present invention raspberry glycosides, mogrosides, maple extract, dihydrokiwifruit lactone, strawberry aldehyde, etc., any two or two of them can be selected according to the cigarette style feature design
  • other flavor components can also be selected for blending with raspberry glycosides according to the needs of the flavor of the cigarette style.
  • the pyrolysis product contains characteristic aroma components such as raspberry ketone in a relatively high content. While raspberry ketone is volatile and unstable at room temperature, raspberry glucoside is stable at room temperature, which ensures the stability of tobacco flavor during storage and transportation.
  • the characteristic aroma of raspberry and blueberry is rich and rich during smoking, and the blending and use of other flavor ingredients ensures the characteristic aroma of mainstream smoke and sidestream smoke, which can improve brand recognition and avoid the phenomenon of homogenization of Chinese-style cigarette products.
  • the flavor dispersion comprising raspberry glycosides of the present invention can be added to cigarette paper or cut tobacco to improve the sensory effect of the cigarette aroma of sidestream smoke.
  • the main and side-stream smoke components of the flavor dispersion comprising raspberry glycosides of the present invention all have great changes, especially the content of the characteristic flavor of raspberry ketone in the side-stream smoke. significantly higher.
  • the characteristic aroma of raspberry ketone in sidestream smoke can bring pleasant smell to the surrounding non-smokers and create a better environment for non-smokers.
  • the flavor dispersion including raspberry glycosides of the present invention can also be used in reconstituted tobacco leaves, and can also improve the characteristic flavor of mainstream smoke and sidestream smoke.
  • natural plants and their extracts are mainly used as flavor additives.
  • Natural plant flavor substances have the characteristics of imparting a unique aroma to cigarettes and improving the smoking quality of cigarettes, and are widely used in cigarette formulations of reconstituted tobacco leaves.
  • the spice dispersion including raspberry glycosides of the present invention can also be used in reconstituted tobacco leaves, and can also make the reconstituted tobacco leaves have the functions of unique aroma and rhythm, improve the smoking quality of cigarettes, and more effectively improve the utilization rate of raw materials of cigarette leaves. Reduce cigarette production costs.
  • the method for enhancing the aroma of cigarette products by the aroma dispersion comprising raspberry glycosides of the present invention is simple.
  • the flavors and fragrances in the prior art, such as raspberry ketone, are insoluble in water, while raspberry glycosides are soluble in water, and are more environmentally friendly when used in cigarettes.
  • the flavoring method of the present invention is more controllable, and the flavoring is more uniform.
  • the selected characteristic aroma does not depend on the formula of leaf group, which is beneficial to reduce the difficulty of formula of leaf group and fragrance.
  • the quality of the off-site processed products of cigarette brands is more guaranteed; at the same time, the use value of low-grade tobacco leaves is improved. Used in cigarette paper to reduce the dependence of high-grade cigarettes on high-priced sesame pulp cigarette paper.
  • Figure 1 shows the molecular formula of raspberry.
  • Figure 2 is the three-dimensional structural formula of raspberry.
  • Figure 3 is a thermogravimetric diagram of raspberry glycosides.
  • the gas chromatography injection port was connected, and the cracked products were separated by gas chromatography and identified by mass spectrometry. If the cracking products do not indicate the matching degree is greater than 800, they are qualitatively searched by the NIST98 standard library, and semi-quantitative analysis of the thermal cracking products is carried out by the peak area normalization method for substances with a peak area greater than 0.1%. (The pyrolysis of each raspberry glycoside sample needs to be done three times, with three temperature ranges, simulating the smoldering temperature of 350°C for heated cigarettes and the smoldering temperature of 600°C for conventional cigarettes and the smoking temperature of 900°C respectively)
  • the carrier gas is He, the flow rate is set to: 1.0 mL/min; the temperature of the injection port: 230 °C; The temperature was raised to 280 °C for 10 min (maintained for 10 min); the split ratio was 1:10; the mass spectrometry conditions: the interface temperature was 230 °C; the temperature of the electrospray ionization source (EI): 250 °C; the ionization energy: 70 eV; 500u.
  • EI electrospray ionization source
  • thermogravimetric analysis method The steps of the thermogravimetric analysis method are:
  • Ketones 65.45%, aldehydes 1.50%, acids 1.23%.
  • raspberry ketone 65.45%
  • p-hydroxybenzaldehyde 1.04%
  • stearic acid 0.67%
  • palmitic acid 0.56%
  • 5-hydroxymethylfurfural 0.46%
  • Others are mainly amine compounds, including 1-methylpentylamine, N-methylethylenediamine, 2-octylamine, 1,3-dimethylpentylamine and N-(2-methoxyethyl) ) methylamine.
  • Figure 3 shows the thermogravimetric results of raspberry glycosides. It can be seen from Figure 3 that the raspberry glucoside sample begins to lose mass from 220 °C, which is due to the breakage of the glycosidic bond, resulting in the formation of raspberry ketones, allose, and glucose ketones; when the temperature is further increased, the resulting raspberry ketones Ketones are pyrolyzed and sublimated, the mass loss rate is the largest, and some of the primary cracking components are further cracked, and the branches such as methoxy, ethoxy and carbonyl on the aromatic ring are removed, and some branches are oxidized to macromolecules such as stearic acid and palmitic acid.
  • Example 1 use of flavor dispersions comprising raspberry in cigarette paper
  • the mass parts of the fragrance formula are as follows: 8 g of raspberry glycosides, 2 g of mogroside, and a small amount of fillers and flame retardants, which are dissolved in 100 g of water to form a fragrance dispersion containing raspberry glycosides.
  • the obtained raspberry-containing flavor dispersion was coated on ordinary cigarette paper and dried, the gram weight of the obtained cigarette paper was 38 g/m 2 and the air permeability was 60 Coresta (CU).
  • the flavor content in the cigarette paper accounts for 0.5 wt % of the cigarette paper.
  • the spice formula in this embodiment is: 7g of raspberry glycosides, 3g of mogrosides, 0.5g of maple extract, and 0.1g of dihydrokiwifruit lactone.
  • the gram weight of the obtained cigarette paper was 30 g/m 2 and the air permeability was 50 CU.
  • the flavor content in the cigarette paper accounts for 0.8 wt % of the cigarette paper.
  • Example 2 The same as Example 1, the difference is the spice formula.
  • the spice formula of this embodiment the mass parts are: raspberry glycoside 4g, mogroside 4g, strawberry aldehyde 0.2g.
  • the gram weight of the obtained cigarette paper was 35 g/m 2 and the air permeability was 60 CU.
  • the flavor content in the cigarette paper accounts for 0.4 wt % of the cigarette paper.
  • the spice formula of this embodiment, the mass parts are: raspberry glycoside 3g, mogroside 5g, maple maple extract 0.5g, strawberry aldehyde 0.2g.
  • the gram weight of the obtained cigarette paper was 33 g/m 2 and the air permeability was 50 CU.
  • the flavor content in the cigarette paper accounts for 0.7 wt % of the cigarette paper.
  • Example 1 The cigarette paper of Example 1 and the normal cigarette paper of the control sample were analyzed and tested. Analysis method: using pyrolysis analysis and cigarette smoke composition analysis methods
  • Pyrolysis heating program initial temperature 50 °C, rising to 30 °C/s to set the pyrolysis temperature to 350 °C, 600 °C and 900 °C, each holding for 5s; pyrolysis atmosphere: 9:91 (V/V) oxygen/nitrogen Mixed gas; gas flow rate: 70mL/min; temperature of valve box of pyrolyzer: 280°C; temperature of transmission line of pyrolyzer: 280°C; temperature of cold trap trapping: -60°C; The temperature was raised to 280°C; cold trap system: silica glass wool with a length of about 2 cm was filled in the middle position of the stainless steel tube from both ends to the center position.
  • the chromatographic column is an elastic quartz capillary column; the stationary phase is 5% phenyl-95% methyl polysiloxane; the specification is [60m (length) ⁇ 0.25 mm (inner diameter) ⁇ 1.0 ⁇ m (film thickness)]; carrier gas flow , 1.5mL/min; split ratio, 100:1;; heating program, the initial temperature was 50 °C, maintained for 4 min, increased to 200 °C at a rate of 4 °C/min, and then increased to 280 °C at a rate of 10 °C/min, Hold for 15min; mass spectrum transmission line temperature: 280°C; ion source temperature, 230°C; quadrupole temperature, 150°C; mass scanning range, 29 ⁇ 450amu;
  • the sample mass was used for peak area correction, and the NIST 2014 mass spectral library was used for search and characterization.
  • the cigarettes used were first equilibrated under the conditions of (22 ⁇ 1) °C and relative humidity (60 ⁇ 2)% for 48 hours, and then sorted by weight and suction resistance to pick out uniform test cigarettes.
  • Smoking cigarettes with SM405-SV side-flow smoking machine the specific method refers to YC/T 185-2004.
  • Each glass fiber filter collects sidestream smoke from 4 cigarettes. Remove the fishtail cover, take 20 mL of methanol, and clean the fishtail cover with a dropper. The methanol solution was collected in a 100 mL Erlenmeyer flask. The collected methanol solution was vacuumed (55° C., 300 mbar), and the internal standard solution was added, which was directly analyzed by GC/MS.
  • the sample cigarettes were equilibrated in an environment of (22 ⁇ 1) °C and relative humidity of (60 ⁇ 2)% for 48 hours, and cigarettes with (average mass ⁇ 0.015) g and (average resistance to draw ⁇ 49) Pa were selected as test samples .
  • the Cambridge filter for capturing the particulate matter in mainstream smoke of 10 cigarettes was put into a 4mL sample bottle, 3mL of dichloromethane extractant was added, and 100 ⁇ L of internal standard solution (2mg/mL) was accurately added, sealed, and ultrasonically extracted for 30min , take the extract, filter through a 0.45 ⁇ m microporous membrane, conduct GC-MS analysis on the filtrate, select ion monitoring (SIM) quantitative analysis to detect the target components.
  • SIM select ion monitoring
  • the internal standard solution was a double internal standard solution of deuterated benzene and phenethyl acetate.
  • the DB-624 column method uses deuterated benzene as the internal standard
  • the DB-5MS column method uses phenethyl acetate as the internal standard.
  • Program temperature Injection volume: 1 ⁇ L; inlet temperature: 290°C; split ratio: 10:1; carrier gas: He, flow rate: 1.5mL/min; transfer line temperature: 290°C; ionization method: EI; ion source temperature: 230°C ; Ionization energy: 70eV; quadrupole temperature: 150°C; mass scan range of mass spectrometry: 26-400amu; monitoring mode: full scan mode and selected ion scan mode.
  • Timed events CH2Cl2 , 0 min detector on; 5 min detector off; 6 min detector on; CH3OH, 0 min detector on; 4 min detector off; 5 min detector on.
  • Program temperature Injection volume: 1 ⁇ L; inlet temperature: 220 °C; split ratio: 10:1; carrier gas: He, flow rate: 1.0 mL/min; transfer line temperature: 240 °C; ionization method: EI; ion source temperature: 230 °C ; Ionization energy: 70eV; quadrupole temperature: 150°C; mass scanning range of mass spectrometry: 20-350amu; monitoring mode: full scan mode and selected ion scan mode.
  • Timed events Dichloromethane, 0min detector on; 12:10min detector off; 13:90min detector on; methanol, 0min detector on; 11:70min detector off; 13:00min detector on.
  • the cigarette paper pyrolysis product of Example 1 has components such as raspberry ketone, guaiacol, p-hydroxybenzaldehyde detected, indicating that the added fragrance has occurred at 350 ° C.
  • raspberry ketone is the characteristic pyrolysis product of raspberry glycosides
  • guaiacol is the characteristic pyrolysis product of mogroside.
  • the types of components detected in the cigarette paper of Example 1 were the same, but the relative proportions changed; at 600°C, the detected content of raspberry ketone was the highest, and the detected amount of guaiacol also increased with the temperature. and increase.
  • test results of the cigarette paper of Examples 2-4 are similar to the test results of the cigarette paper of Example 1, especially the content of raspberry ketone and guaiacol in the main and side flow smoke is also significantly higher.
  • Example 6 use of flavor dispersions comprising raspberry in cut tobacco
  • the fragrance formula is the same as that of Example 1.
  • the spice dispersion containing raspberry glycosides is sprayed into the cut tobacco and dried to a suitable moisture content, so that the cut tobacco can be added.
  • the content of flavor in the cut tobacco accounts for 0.05wt%.
  • Example 7 use of flavor dispersions comprising raspberry in cut tobacco
  • the fragrance formula is the same as that of Example 2. Among them, the content of flavoring accounts for 0.07wt% of the cut tobacco.
  • Example 8 use of flavor dispersion comprising raspberry in cut tobacco
  • the fragrance formula is the same as that of Example 3. Among them, the content of flavors accounts for 0.03wt% of the cut tobacco.
  • Example 9 use of flavor dispersion comprising raspberry in cut tobacco
  • the fragrance formula is the same as that in Implementation 4. Among them, the content of spices accounts for 0.06wt% of the cut tobacco.
  • Example 6 The shredded tobacco of Example 6 and the cigarettes rolled into it were tested, and the test method and conditions were the same as those of Example 5.
  • the test results are as follows: the distribution ratio of raspberry ketone, the pyrolysis component of raspberry glycoside in the main and side flow smoke of cigarettes, in the main and side flow smoke is 1:4.05, and the pyrolysis component of mogroside is guaiacol in the main and side flow smoke.
  • the distribution ratio in the main and side flow flue gas is 1:3.19.
  • the results are basically similar to the test results of Example 5.
  • the side-flow smoke of the cigarettes prepared by adding the cigarettes of the present invention can also clearly feel the characteristic aromas such as raspberries and blueberries brought by the added spices, and the sensory intensity is obviously stronger than that of mainstream smoke, which brings great benefits to non-smokers. Better pleasant smell.
  • Example 11 use of flavor dispersions comprising raspberry in reconstituted tobacco leaves.
  • the fragrance formula is the same as that of Example 1. After the spice dispersion containing raspberry is sprayed into the reconstituted tobacco shreds and dried, the reconstituted shredded tobacco leaves are obtained. Among them, the content of flavors accounts for 0.5wt% of the cut tobacco.
  • Example 10 The test method and conditions are the same as in Example 10.
  • the test results are as follows: the distribution ratio of raspberry ketone, the pyrolysis component of raspberry glycoside in the main and side flow smoke of cigarettes, in the main and side flow smoke is 1:4.58, and the pyrolysis component of mogroside is guaiacol in the main and side flow smoke.
  • the distribution ratio in the main and side flow flue gas is 1:3.92.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Botany (AREA)
  • Manufacture Of Tobacco Products (AREA)

Abstract

用树莓苷提高卷烟产品香气的方法，将包括树莓苷的香料分散或溶于溶剂中形成香料分散体，然后添加到卷烟中。使用树莓苷作为潜香香料用于卷烟中，解决了卷烟中的香料不够稳定、风格特征不突出的问题。将包括树莓苷的香料分散体用于卷烟纸、烟丝或再造烟叶中，卷烟中的主流烟气和侧流烟气具有覆盆子酮的特征香。

Description

用树莓苷提高卷烟产品香气的方法 技术领域
本发明属于烟草技术领域，具体涉及用树莓苷提高卷烟产品主流烟气抽吸品质和侧流烟气特征烟香的方法。
背景技术
卷烟产品的降焦减害是烟草制品发展的趋势。降焦减害必然带来烟草香气的不足，影响消费者体验。而配方加香是提高烟草产品抽吸体验的有效方法。现有技术中的将常规香精香料加入到烟丝、卷烟纸以及再造烟叶中等有较多的报道。但现有技术用于加香的常规香精香料在在线加香和产品运输储存过程中存在挥发逸散的情况，这会影响香精香料有效加香率、带来卷烟产品香气稳定性差的问题。另外，现有技术的烟草加香技术主要集中在调节或提高主流烟气的抽吸感官效果上，而不关注侧流烟气烟香的感官效果；而侧流烟气烟香能带来愉悦的气味，给周围非吸烟人群创造更好的气味环境。第三，现有技术的香精香料不溶于水，如香料覆盆子酮只能溶于乙醚或挥发性油中，给烟草的加香带来安全隐患。
树莓苷是树莓中的一种功能性成分，树莓苷的化学名称为4-丁酮基苯基-β-D-吡喃葡萄糖苷或覆盆子酮-β-D-吡喃葡萄糖苷，分子式为C 16H 22O 7，CAS号是38963-94-9。树莓苷的结构式如附图1和图2所示。树莓苷的状态为白色或类白色结晶性粉末，易溶于水、乙醇等极性溶剂，常温下没有气味。树莓苷具有特殊的生理功能和生物学活性，可以有效阻碍酪氨酸酶的形成，抑制黑色素，现有技术的报道树莓苷的用途主要用于高级美白、祛斑、抗衰老及调理性的化妆品中。
将树莓苷用于烟草中以提高卷烟产品香气的用途还没有报道。
发明内容
本发明旨在使用包括树莓苷在内的香料分散或溶于溶剂中形成香料分散体，然后添加到卷烟中，以提升卷烟产品的辨识度、提高测流烟香的特征感改善主流烟气抽吸品质、拓宽产品风格的丰富性，并解决现有技术中香精香料不够稳定进而影响卷烟质量稳定性的问题。
本发明的技术方案如下：
本发明公开了一种用树莓苷提高卷烟产品香气的方法，将包括树莓苷的香料分散或溶于溶剂中形成香料分散体，然后添加到卷烟中。
优选地，将所述香料分散体添加到卷烟纸、烟丝或再造烟叶中以提高侧流烟气特征烟香和/或改善主流烟气抽吸品质。
优选地，所述溶剂为水、乙醇或两者的混合物。
优选地，所述香料分散体中还包括其他香料成份。
优选地，其他香料成份包括罗汉果甜苷、枫槭浸膏、二氢猕猴桃内酯、草莓醛中的一种或几种。
优选地，所述香料分散体中的香料包含：①树莓苷和罗汉果甜苷，两者的质量比为(2-8):(1-3)；或②树莓苷、罗汉果甜苷、枫槭浸膏和二氢猕猴桃内酯，四者的质量比为(2-8):(1-3):(0.5-1):(0.05-0.1)；或③树莓苷、罗汉果甜和苷草莓醛，三者的质量比为(2-5):(2-5):(0.1-0.3)；或④树莓苷、罗汉果甜苷、枫槭浸膏和草莓醛，四者的质量比为(2-5):(2-5):(0.5-1):(0.1-0.3)。
优选地，所述香料分散体中还包括填料和助燃剂。
优选地，所述填料为轻质碳酸钙。
优选地，所述助燃剂为有机酸金属盐，所述有机酸金属盐为柠檬酸钾、苹果酸钾、乳酸钾、乙酸钾中的一种或两种以上的组合。
优选地，所述香料分散体涂覆到卷烟纸上，香料的涂布率是0.1wt％～1wt％(即香料占卷烟纸干重的重量百分比)，得到的卷烟纸的定量为28-38g/cm 2，透气度为30-100科雷斯塔。
本发明的有益效果：
1、本发明首次使用树莓苷作为潜香香料用于卷烟中。本发明将包括树莓苷在内的香料分散体加入到卷烟中，解决了卷烟中的香料不够稳定、风格特征不突出的问题。
2、本发明的树莓苷为热稳定型潜香香料，在再造烟叶、卷烟纸或卷烟产品的储存和运输过程中该香料非常稳定，闻不到气味。加热或点燃抽吸时，可释放出覆盆子酮特征成分，产生树莓、蓝莓特征香气，具有与烟草本香融合协调的功 能效果，可调配出凸显浆果风格特征的香味，提高了卷烟感官抽吸品质。
3、本发明选定的其他辅助香料成份：树莓苷、罗汉果甜苷、枫槭浸膏、二氢猕猴桃内酯、草莓醛等，可根据卷烟风格特征设计选择其中的任意两种或两种以上，与树莓苷灵活调配使用，进一步凸显不同卷烟风格特征的香味，提高了感官抽吸品质。除上述的香料成份，根据卷烟风格特征的香味的需要也可选择其他香料成份与树莓苷调配使用。
4、本发明的包括树莓苷的香料分散体，热解产物中含有较高含量的覆盆子酮等特征香成分。而覆盆子酮常温下易挥发不稳定，但树莓苷常温下稳定，这就保证了烟草在储存和运输过程中香料稳定。而抽吸时树莓、蓝莓特征香气丰富浓郁，与其他香料成份调配使用保证了主流烟气和侧流烟气具有的特征香味，能提高品牌识别度，避免中式卷烟产品同质化现象。
5、本发明的包括树莓苷的香料分散体加入到卷烟纸或烟丝中可以提高侧流烟气的烟香的感官效果。与普通加香卷烟对照样相比，本发明的包括树莓苷的香料分散体的主侧流烟气成分均有较大变化，特别是覆盆子酮的特征香味在侧流烟气中的含量明显较高。用于卷烟成品抽吸时，侧流烟气的覆盆子酮的特征香能给周围的非吸烟人群带来愉悦的气味，为非吸烟人群创造更好的环境。
6、本发明的包括树莓苷的香料分散体也可以用于再造烟叶中，同样可以提高主流烟气和侧流烟气的特征香味。目前在传统再造烟叶生产中，主要使用天然植物及其提取物作为香味添加剂，天然植物香味物质具有赋予卷烟独特香气韵调、提高卷烟抽吸品质的特性而被广泛应用于再造烟叶的卷烟配方中。本发明的包括树莓苷的香料分散体也可以用于再造烟叶中，同样可以使再造烟叶具有独特香气韵调、提高卷烟抽吸品质的功能，更加有效地提高卷烟叶组原料的利用率，降低卷烟生产成本。
7、本发明的包括树莓苷的香料分散体用于提高卷烟产品香气的方法简单。现有技术的香精香料如覆盆子酮不溶于水，而树莓苷能溶于水中，用于卷烟中更符合环保要求。本发明的加香方式相比卷烟的传统加料加香方式更可控，加香更均匀。选择的特征香不依赖于叶组配方，有利于降低叶组、料香配方难度。卷烟品牌的异地加工产品质量更有保障；同时提高了低次等烟叶的使用价值。用于卷烟纸中降低了高档卷烟对高价麻浆卷烟纸的依赖。
附图说明
图1为树莓苷的分子式。
图2为树莓苷的立体结构式。
图3为树莓苷的热重图。
具体实施方式
为了使本发明的目的、技术方案及优点更加清楚明白，下面结合具体实施例，进一步阐述本发明。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。下列实施例中未注明具体条件的实验方法，通常按照常规条件。除非另外说明，所述百分比和份数按质量计算。
树莓苷的热稳定性及热裂解行为研究。树莓苷的热裂解步骤如下：
精确称取1.5mg树莓苷加入到裂解专用石英管中，然后将石英管置于热裂解仪的加热丝中，热裂解氛围：空气；总裂解气流速：70mL/min；热裂解探头(热解头)升温程序为：①50℃起始(保持5s)以10℃/s升至350℃(保持5s)；②50℃起始(保持5s)以10℃/s升至600℃(保持5s)；③50℃起始(保持5s)以10℃/s升至900℃(保持5s)。完毕后，连接气相色谱进样口，裂解产物经气相色谱分离后用质谱鉴定。裂解产物若不标明匹配度的均为大于800，经NIST98标准谱库检索定性，对峰面积大于0.1％的物质通过峰面积归一法对热裂解产物进行半定量分析。(热裂解每个树莓苷样品需要做三次，三个温度区间，分别模拟加热卷烟350℃和常规卷烟的阴燃温度600℃和抽吸温度900℃)
气相色谱-质谱条件为：
载气为He，流量设置为：1.0mL/min；进样口温度：230℃；升温程序：50℃(保持5min)以10℃/min升高至100℃(保持1min)，以15℃/min升高至280℃(保持10min)；分流比为1:10；质谱条件：接口温度为230℃；电喷雾离子源(EI)温度：250℃；电离能量：70eV；质量扫描范围：35～500u。
热重分析方法步骤为：
称取(5.00±0.05)mg树莓苷样品置于热重铂坩埚内。在50mL/min空气流量下，升温程序为：30℃以10℃/min升至900℃(10min)。做DSC、TG/DTG分析，数据整理归纳分析。
树莓苷的热稳定性及热裂解的结果为：
如下表1所示和图3所示，对树莓苷的热裂解成分分析表明，在350℃时热裂解共检出化合物17种，占总峰面积62.69％。酮类50.11％，醛类2.91％，酸类1.07％，酚类0.76％，以及其他类7.58％。其他类中主要是糖类化合物，包括D-阿洛糖和1,6-脱水-β-D-葡萄糖。其中相对含量较高的有覆盆子酮(47.64％)、D-阿洛糖(7.01％)、左旋葡萄糖酮(1.84％)、5-羟甲基糠醛(1.28％)、糠醛(0.84％)、对羟基苯甲醛(0.78％)。
在600℃时热裂解共检出化合物5种，占总峰面积68.18％。酮类65.45％，醛类1.50％，酸类1.23％。其中相对含量较高的有覆盆子酮(65.45％)、对羟基苯甲醛(1.04％)、硬脂酸(0.67％)、棕榈酸(0.56％)、5-羟甲基糠醛(0.46％)。
在900℃时热裂解共检出化合物18种，占总峰面积82.74％。酮类79.88％，醛类0.66％，酸类0.73％，酚类0.30％，以及其他类1.06％。其他类中主要是胺类化合物，包括1-甲基戊胺、N-甲基乙二胺、2-辛胺、1,3-二甲基戊胺和N-(2-甲氧基乙基)甲基胺。其中相对含量较高的有覆盆子酮(78.75％)、3,5-二羟基-2-甲基吡喃-4-酮(0.74％)、2,3-二氢苯并呋喃(0.67％)、对羟基苯甲醛(0.66％)、棕榈酸(0.61％)。
可以看出，随着裂解温度升高，树莓苷裂解产生的致香物质的峰面积占比是增加趋势，酮类物质占比增加，尤其是覆盆子酮的占比显著增加。醛类、酸类和酚类占比下降，胺类物质在900℃时热裂解出现。
上述结果说明，不同温度下树莓苷都可以热裂解产生特征香气成分覆盆子酮，且裂解温度越高，覆盆子酮的含量越大，这个特点是大部分糖苷类潜香物质所不具备的，很多其它结构的糖苷类化合物在热裂解时，香气成分配基会深度热裂解为非特征气味成分，很少能得到结构性质保持的香气配基。作为对比，表2列出了橙花醇葡萄糖苷在不同温度下的热裂解情况，结果显示，配基橙花醇在不同温度下结构均不能保持，被进一步热裂解成乙酰胺了。故橙花醇葡萄糖苷热裂解不产生橙花特征气味。
图3所示树莓苷的热重结果。由图3可以看出，220℃起树莓苷样品开始出现质量损失，这是由于糖苷键的断裂，生成覆盆子酮和阿洛糖、葡萄糖酮类；当温度进一步升高，生成的覆盆子酮热解升华，质量损失率最大，部分初级裂解成 分进一步裂解，脱掉芳香环上甲氧基、乙氧基和羰基等等支链，部分支链氧化成硬脂酸、棕榈酸等大分子酸类，部分支链和芳香环氧化成糠醛、5-羟甲基糠醛等等芳香类物质；温度继续升高，370℃左右剩余香气物质开始出现碳化，约580℃时，香气物质完全碳化，质量不再变化。
表1 树莓苷在不同温度下的热裂解结果
Figure PCTCN2021083058-appb-000001
表2 橙花醇葡萄糖苷在不同温度下的热裂解结果
Figure PCTCN2021083058-appb-000002
实施例1，将包括树莓苷的香料分散体用于卷烟纸中
将香料配方质量份如下：树莓苷8g，罗汉果甜苷2g，同时含有少量的填料和阻燃剂，溶于100g水中形成含树莓苷的香料分散体。将得到的含树莓苷的香料分散体涂布到普通卷烟纸上干燥后，得到的卷烟纸的克重为38g/m 2，透气度为60科雷斯塔(CU)。其中的香料含量占卷烟纸的0.5wt％。
实施例2
同实施例1，不同之处为香料配方，本实施例的香料配方，质量份为：树莓苷7g，罗汉果甜苷3g，枫槭浸膏0.5g，二氢猕猴桃内酯0.1g。得到的卷烟纸克重为30g/m 2，透气度为50CU。其中的香料含量占卷烟纸的0.8wt％。
实施例3
同实施例1，不同之处为香料配方，本实施例的香料配方，质量份为：树莓苷4g，罗汉果甜苷4g，草莓醛0.2g。得到的卷烟纸克重35g/m 2，透气度为60CU。其中的香料含量占卷烟纸的0.4wt％。
实施例4
同实施例1，不同之处为香料配方，本实施例的香料配方，质量份为：树莓苷3g，罗汉果甜苷5g，枫槭浸膏0.5g，草莓醛0.2g。得到的卷烟纸克重33g/m 2，透气度为50CU。其中的香料含量占卷烟纸的0.7wt％。
实施例5：测试
将实施例1的卷烟纸和对照样普通卷烟纸进行分析测试。分析方法：采用热解分析和卷烟烟气成分分析方法
1、热解分析方法
参考《YQ/T-792016烟草添加剂热裂解技术规程》进行热解，具体如下：
(1)热解条件
热解升温程序：初始温度50℃，以30℃/s升至设置热解温度为350℃、600℃和900℃，各保持5s；热解氛围：9:91(V/V)氧/氮混合气；气体流量：70mL/min； 热解仪阀箱温度：280℃；解仪传输线温度：280℃；冷阱捕集温度：-60℃；冷阱进样条件：在5min内由-60℃升至280℃；冷阱系统：在不锈钢管中间位置从两端装填至中心位置约2cm长的硅氧化玻璃棉。
(2)GC-MS条件
色谱柱为弹性石英毛细管柱；固定相为5％苯基-95％甲基聚硅氧烷；规格为[60m(长度)×0.25mm(内径)×1.0μm(膜厚)]；载气流量，1.5mL/min；分流比，100:1；；升温程序，初始温度50℃，保持4min，以4℃/min的速率升至200℃，再以10℃/min的速率升至280℃，保持15min；质谱传输线温度：280℃；离子源温度，230℃；四极杆温度，150℃；质量扫描范围，29～450amu；
(3)数据处理
采用样品质量进行峰面积校正，并应用NIST 2014质谱谱库进行检索定性。
2、烟气分析方法；将实施例1的卷烟纸和普通卷烟纸制成烟支，除卷烟纸外，其他如烟丝、滤嘴等完全相同。
(A)仪器和试剂
Cerulean SM405-SV型侧流吸烟机；Agilent 6890－5973气相色谱－质谱联用仪；Buchi R-210型旋转蒸发仪旋转蒸发仪；弹性石英毛细管色谱柱：DB-5MS 30m×0.25mm×0.25μm；甲醇、二氯甲烷、氘代苯和乙酸苯乙酯均为色谱纯。
(B)侧流烟气总粒相物的收集和预处理
所用烟支首先在(22±1)℃、相对湿度(60±2)％条件下平衡48h，然后经重量及吸阻分选，挑出均匀一致的试验烟支。用SM405-SV型侧流吸烟机抽吸卷烟，具体方法参考YC/T 185-2004。每张玻璃纤维滤片收集4支卷烟侧流烟气。取下鱼尾罩，取20mL甲醇，用滴管吸取对鱼尾罩进行清洗。用100mL三角瓶收集甲醇溶液。收集到的甲醇溶液在抽真空条件下(55℃，300mbar)，加入内标溶液，直接用GC/MS分析。
(C)主流烟气总粒相物的收集和预处理
a.烟气捕集：
将样品卷烟烟支在(22±1)℃、相对湿度(60±2)％的环境中平衡48h，挑选(平均质量±0.015)g和(平均吸阻±49)Pa的烟支作为测试样品。用直线型吸烟机抽吸卷烟烟支，每组抽吸10支，用直径为44mm剑桥滤片捕集卷烟主流烟气粒相物， 在捕集器后面接两个串联的吸收瓶，每个吸收瓶装10mL甲醇溶液，并在低温(干冰/异丙醇浴)条件下捕集主流烟气气相成分。
b.粒相组分分析
捕集10支卷烟烟支主流烟气粒相物的剑桥滤片放入4mL样品瓶中，加入3mL二氯甲烷萃取剂，并准确加入100μL内标溶液(2mg/mL)，密封，超声萃取30min，取萃取液，经0.45μm微孔滤膜过滤，滤液进行GC-MS分析，选择离子监测(SIM)定量分析检测目标成分。
c.气相组分分析
烟支抽吸后，用洗耳球分别对两个吸收瓶中的吸收管抽吸5次进行清洗，每个吸收瓶中准确加入100μL内标溶液，搅拌均匀后，各取两个吸收瓶中1mL溶液混匀进行GC/MS分析。内标溶液为氘代苯和乙酸苯乙酯的双内标溶液。DB-624色谱柱方法使用氘代苯为内标，DB-5MS色谱柱方法使用乙酸苯乙酯为内标。
d.色谱质谱分析
气粒相样品取双份，分别在DB-5MS和DB-624两根柱子上进样分析，具体色谱质谱分析条件如下：DB-5MS(60m×1.0μm×0.25mm)方法：
程序升温：
Figure PCTCN2021083058-appb-000003
进样量：1μL；进样口温度：290℃；分流比：10：1；载气：He，流速：1.5mL/min；传输线温度：290℃；电离方式：EI；离子源温度：230℃；电离能量：70eV；四极杆温度：150℃；质谱质量扫描范围：26～400amu；监测模式：全扫描模式和选择离子扫描模式。
定时事件：CH 2Cl 2，0min检测器打开；5min检测器关闭；6min检测器打开；CH 3OH，0min检测器打开；4min检测器关闭；5min检测器打开。
DB-624(60m×1.4μm×0.25mm)方法：
程序升温：
Figure PCTCN2021083058-appb-000004
进样量：1μL；进样口温度：220℃；分流比：10：1；载气：He，流速：1.0mL/min；传输线温度：240℃；电离方式：EI；离子源温度：230℃；电离能量：70eV；四极杆温度：150℃；质谱质量扫描范围：20～350amu；监测模式：全扫描模式和选择离子扫描模式。
定时事件：二氯甲烷，0min检测器打开；12:10min检测器关闭；13:90min 检测器打开；甲醇，0min检测器打开；11:70min检测器关闭；13:00min检测器打开。
3、检测结果如下：
实施例1的卷烟纸不同温度热解结果见下表3。
表3 实施例1的卷烟纸不同温度热解结果
Figure PCTCN2021083058-appb-000005
Figure PCTCN2021083058-appb-000006
由表3可以看出，在350℃时，实施例1的卷烟纸热解产物中有覆盆子酮、愈创木酚、对羟基苯甲醛等成分检出，表明添加的香料在350℃已发生热解反应，覆盆子酮是树莓苷的特征热解产物，愈创木酚是罗汉果甜苷的特征热解产物。600℃和在900℃时实施例1的卷烟纸所检出成分种类相同，相对比例有所变化；600℃时覆盆子酮检出含量最高，而愈创木酚检出量也随温度升高而增加。
900℃下比较实施例1的加香卷烟纸和对照样普通卷烟纸热解产物差异。 表4 实施例1的卷烟纸与对照样900℃热解比较
Figure PCTCN2021083058-appb-000007
Figure PCTCN2021083058-appb-000008
由表4可知，在900℃时，实施例1的加香卷烟纸的有愈创木酚、对羟基苯甲醛、覆盆子酮、棕榈酸检出，对照样则无这四种成分检出。
除此之外，实施例1的加香卷烟纸的其它热解产物与对照样也有较大差异。实施例1的加香卷烟纸的热解产物中甲酸、羟基丙酮、羟基乙醛、丁二醛、2,3-二羟基苯甲醛、双脱水吡喃型葡萄糖等成分含量较高，而环戊酮、对二甲苯、二甲基苯酚等成分的含量较低。
烟支的主流与侧流烟气的分析结果相似。相对于对照样，实施例1的加香卷烟纸制备的烟支在主流与侧流烟气均检出覆盆子酮、愈创木酚等特征成分，而对照样烟支则未发现这些成分。实施例1的加香卷烟纸的烟支主侧流烟气中特征香气成分的对比情况见下表5。
表5 烟支的主侧流烟气特征成分对比(μg/支)
化合物 主流烟气 侧流烟气 比值
覆盆子酮 1.31 6.80 1:5.19
愈创木酚 0.27 1.17 1:4.33
经专家对烟支嗅辨评价可知，在侧流香气中覆盆子酮和愈创木酚的树莓、蓝莓等的特征香表现的更为明显。
由以上测试可知，实施例1的加香卷烟纸的热解产物中检出覆盆子酮、愈创木酚等特征成分，并且烟支在主侧流烟气中含量有较大差异。树莓苷热裂解成分覆盆子酮在主、侧流烟气中的分配比例为1:5.19，罗汉果甜苷的热解成分愈创木酚在主、侧流烟气中的分配比例为1:4.33。因此本发明的加香卷烟纸制备的烟支的侧流烟气可以明显感受到所添加香料带来的树莓、蓝莓等的特征香，感官强度明显强于主流烟气。侧流烟气中的这些香味能给周围的非吸烟人群带来愉悦的气味，为非吸烟人群创造更好的环境。
实施例2-4的卷烟纸的测试与实施例1的卷烟纸的测试结果相似，特别是覆盆子酮和愈创木酚在主、侧流烟气中含量也明显较高。
实施例6，将包括树莓苷的香料分散体用于烟丝中
香料配方同实施例1。将含树莓苷的香料分散体喷洒到烟丝中经干燥到合适含水率，得加香烟丝。其中的香料含量占烟丝的0.05wt％。
实施例7，将包括树莓苷的香料分散体用于烟丝中
香料配方同实施例2。其中的香料含量占烟丝的0.07wt％。
实施例8，将包括树莓苷的香料分散体用于烟丝中
香料配方同实施例3。其中的香料含量占烟丝的0.03wt％。
实施例9，将包括树莓苷的香料分散体用于烟丝中
香料配方同实施4。其中的香料含量占烟丝的0.06wt％。
实施例10：测试
将实施例6的烟丝及烟丝卷成的烟支进行测试，测试方法和条件同实施例5。测试结果为：烟支在主侧流烟气中树莓苷热裂解成分覆盆子酮在主、侧流烟气中的分配比例为1:4.05，罗汉果甜苷的热解成分愈创木酚在主、侧流烟气中的分配比例为1:3.19。结果基本与实施例5的测试结果相似。
因此本发明的加香烟丝制备的烟支的侧流烟气也可以明显感受到所添加香料带来的树莓、蓝莓等特征香，感官强度明显强于主流烟气，为非吸烟人群带来更好的愉悦的气味。
实施例11，将包括树莓苷的香料分散体用于再造烟叶中。
香料配方同实施例1。将含树莓苷的香料分散体喷洒到再造烟叶丝中干燥后，得到再造烟叶丝。其中的香料含量占烟丝的0.5wt％。
测试方法和条件同实施例10。测试结果为：烟支在主侧流烟气中树莓苷热裂解成分覆盆子酮在主、侧流烟气中的分配比例为1:4.58，罗汉果甜苷的热解成分愈创木酚在主、侧流烟气中的分配比例为1:3.92。这说明本发明的包括树莓苷的香料分散体用于再造烟叶中，同样可以使再造烟叶具有独特香气韵调、提高卷烟抽吸品质的功能，更加有效地提高卷烟叶组原料的利用率，降低卷烟生产成本。
以上显示和描述了本发明的基本原理、主要特征和本发明的优点。本领域的技术人员应该了解，本发明不受上述实施例的限制，上述实施例和说明书中描述的只是说明本发明的原理，在不脱离本发明精神和范围的前提下，本发明还会有各种变化和改进，这些变化和改进都落入要求保护的本发明范围内。本发明要求保护范围由所附的权利要求书及其等效物界定。

Claims (10)

  1. 用树莓苷提高卷烟产品香气的方法，其特征在于，将包括树莓苷的香料分散或溶于溶剂中形成香料分散体，然后添加到卷烟中。
  2. 根据权利要求1的方法，其特征在于，将所述香料分散体添加到卷烟纸、烟丝或再造烟叶中以提高侧流烟气特征烟香和/或改善主流烟气抽吸品质。
  3. 根据权利要求1的方法，其特征在于，所述溶剂为水、乙醇或两者的混合物。
  4. 根据权利要求1的方法，其特征在于，所述香料分散体中还包括其他香料成份。
  5. 根据权利要求1的方法，其特征在于，其他香料成份包括罗汉果甜苷、枫槭浸膏、二氢猕猴桃内酯、草莓醛中的一种或几种。
  6. 根据权利要求5的方法，其特征在于，所述香料分散体中的香料包含：①树莓苷和罗汉果甜苷，两者的质量比为(2-8):(1-3)；或②树莓苷、罗汉果甜苷、枫槭浸膏和二氢猕猴桃内酯，四者的质量比为(2-8):(1-3):(0.5-1):(0.05-0.1)；或③树莓苷、罗汉果甜苷和草莓醛，三者的质量比为(2-5):(2-5):(0.1-0.3)；或④树莓苷、罗汉果甜苷、枫槭浸膏和草莓醛，四者的质量比为(2-5):(2-5):(0.5-1):(0.1-0.3)。
  7. 根据权利要求6的方法，其特征在于，所述香料分散体中还包括填料和助燃剂。
  8. 根据权利要求7的方法，其特征在于，所述填料为轻质碳酸钙。
  9. 根据权利要求7的方法，其特征在于，所述助燃剂为有机酸金属盐，所述有机酸金属盐为柠檬酸钾、苹果酸钾、乳酸钾、乙酸钾中的一种或两种以上的组合。
  10. 根据权利要求2的方法，其特征在于，所述香料分散体涂覆到卷烟纸上，香料的占卷烟纸干重的重量比为0.1wt％～1wt％，得到的卷烟纸的定量为28-38g/cm 2，透气度为30-100科雷斯塔。
PCT/CN2021/083058 2021-03-15 2021-03-25 用树莓苷提高卷烟产品香气的方法 WO2022193351A1 (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP21878763.8A EP4085769B1 (en) 2021-03-15 2021-03-25 Method for improving aroma of cigarette product by using raspberry ketone glucoside

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN202110277525.X 2021-03-15
CN202110277525.XA CN113100469B (zh) 2021-03-15 2021-03-15 用树莓苷提高卷烟产品香气的方法

Publications (1)

Publication Number Publication Date
WO2022193351A1 true WO2022193351A1 (zh) 2022-09-22

Family

ID=76711336

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2021/083058 WO2022193351A1 (zh) 2021-03-15 2021-03-25 用树莓苷提高卷烟产品香气的方法

Country Status (3)

Country Link
EP (1) EP4085769B1 (zh)
CN (1) CN113100469B (zh)
WO (1) WO2022193351A1 (zh)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113092650B (zh) * 2021-04-16 2022-04-19 云南中烟工业有限责任公司 一种卷烟纸中树莓苷的检测方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6576247B1 (en) * 1994-11-10 2003-06-10 Kanebo Ltd. And T. Hasegawa Co. Ltd. Sustained-release aromatic and method of detecting micro-organism by using the same
CN103525558A (zh) * 2013-09-27 2014-01-22 福建中烟工业有限责任公司 一种具有果香特征的茶树花香精及其在卷烟中的应用
CN108669637A (zh) * 2018-06-01 2018-10-19 云南中烟工业有限责任公司 一种用于卷烟中的香料添加物的制备方法及用途
CN109123752A (zh) * 2018-10-23 2019-01-04 深圳津丹香生物技术中心有限公司 一种低温雾化烟用香料及其应用
CN109989298A (zh) * 2019-05-10 2019-07-09 云南红塔蓝鹰纸业有限公司 一种花果香型卷烟纸及其制备方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4243823A (en) * 1979-05-15 1981-01-06 International Flavors & Fragrances Inc. 2,6,6-Trimethyl-α-(iso)propenyl-1-cyclohexene-1-methanols and -1,3-cyclohexadiene-1-methanols and organoleptic uses thereof
CN1095350C (zh) * 1999-11-19 2002-12-04 长沙卷烟厂 一种烤烟型低侧流烟气卷烟
CN102408945A (zh) * 2011-07-29 2012-04-11 武汉黄鹤楼香精香料有限公司 一种天然草莓香精及其制备方法
CN106974321B (zh) * 2017-05-23 2019-10-11 安徽中烟工业有限责任公司 一种凸显头口香香气的卷烟及其制作方法
CN107418736B (zh) * 2017-06-21 2020-12-04 武汉黄鹤楼香精香料有限公司 一种烟用香料的制备方法
CN110464043B (zh) * 2019-07-09 2022-01-11 河南中烟工业有限责任公司 用于加热不燃烧卷烟的清香香精及烟草薄片和不燃烧卷烟

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6576247B1 (en) * 1994-11-10 2003-06-10 Kanebo Ltd. And T. Hasegawa Co. Ltd. Sustained-release aromatic and method of detecting micro-organism by using the same
CN103525558A (zh) * 2013-09-27 2014-01-22 福建中烟工业有限责任公司 一种具有果香特征的茶树花香精及其在卷烟中的应用
CN108669637A (zh) * 2018-06-01 2018-10-19 云南中烟工业有限责任公司 一种用于卷烟中的香料添加物的制备方法及用途
CN109123752A (zh) * 2018-10-23 2019-01-04 深圳津丹香生物技术中心有限公司 一种低温雾化烟用香料及其应用
CN109989298A (zh) * 2019-05-10 2019-07-09 云南红塔蓝鹰纸业有限公司 一种花果香型卷烟纸及其制备方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CAS, no. 38963-94-9
TECHNICAL REGULATIONS ON TOBACCO ADDITIVES THERMAL PYROLYSIS, 2016

Also Published As

Publication number Publication date
CN113100469B (zh) 2022-01-28
EP4085769B1 (en) 2023-09-20
EP4085769A4 (en) 2023-01-25
EP4085769A1 (en) 2022-11-09
CN113100469A (zh) 2021-07-13

Similar Documents

Publication Publication Date Title
Zhang et al. HS-SPME and GC/MS volatile component analysis of Yinghong No. 9 dark tea during the pile fermentation process
CN106010789B (zh) 一种基于香料阈值的花香香型烟用香精及其调配方法
CN101224040B (zh) 一种烟用香料及部分替代津巴布韦烟叶的方法
CN106165906A (zh) 一种适用于卷烟制品的麦芽焦甜香香料及其在烟草制品中的应用
CN102140389B (zh) 邻羟基酮类调配香精及其应用
CN102038284A (zh) 一种烟草添加剂及其应用
CN107114821B (zh) 一种热捕集制备烟味香料的装置和方法
CN105686070A (zh) 一种烟草源基础烟味原料的制备方法
WO2022193351A1 (zh) 用树莓苷提高卷烟产品香气的方法
CN106047483B (zh) 一种基于香料阈值的辛香香型烟用香精及其调配方法
CN111827002A (zh) 一种清香型卷烟纸及其制备方法
CN109171004A (zh) 一种复配枫槭浸膏美拉德反应香料、其制备方法及在造纸法再造烟叶中的应用
CN105969521B (zh) 一种基于香料阈值的木香香型烟用香精及其调配方法
CN1360857A (zh) 基于燃烧调香技术的仿生液体烟叶制备方法
CN101343596A (zh) 一种红茶精油及其制备方法和应用
Wei et al. Investigation on fresh bamboo replacing rice husks for brewing light‐aroma Baijiu
CN113349413B (zh) 一种应用于加热卷烟能增香减害的低温馏分的制备方法及其在加热卷烟中的用途
CN113355160B (zh) 一种用于卷烟的椿香型香精及包含该香精的卷烟
CN101444334A (zh) 6-O-乙酰基-2，3，4-三-O-异丁酰基-β-D-吡喃葡萄糖在卷烟中的应用
Yin et al. Study on the effect of potassium lactate additive on the combustion behavior and mainstream smoke of cigarettes
CN108606360B (zh) 一种二酯类烟用香料在卷烟中的应用
CN112796145B (zh) 一种苔清香卷烟纸、其制备方法及用途
CN106085597B (zh) 一种基于香料阈值的脂蜡香型烟用香精及其调配方法
CN109864331A (zh) 一种卷烟香料添加剂及其制备方法
CN110652027B (zh) 用于烟草加香的释放型木糖酯香料合成方法

Legal Events

Date Code Title Description
ENP Entry into the national phase

Ref document number: 2021878763

Country of ref document: EP

Effective date: 20220422

NENP Non-entry into the national phase

Ref country code: DE